Ethanol → HCID 67299291, compound

HRID 1925569Notes

Reaction equation

HRID 1925569 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[C:20]3[N:19]4[CH:21]=[CH:22][CH:23]=[C:18]4[C:17](=[N:24][OH:25])[C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH:3]=1.[CH2:26]([OH:28])[CH3:27].O>C(O)(=O)C.[Zn]>[C:26]([OH:25])(=[O:28])[CH3:27].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[C:20]3[N:19]4[CH:21]=[CH:22][CH:23]=[C:18]4[CH:17]([NH2:24])[C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 86656076HCID 86656076, compound

Product 1

HCID 67299291HCID 67299291, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

In a 100 ml round-bottomed flask, a mixture of 277 mg of 5-quinolin-3-ylpyrrolo[1,2-a]indol-9-one oxime hydrochloride obtained according to the preceding stage, in 5 ml of acetic acid, 5 ml of ethanol and 5 ml of water, is stirred at ambient temperature. 58 mg of powdered zinc are added and the resulting mixture is left to stir for 1.5 hours. A further 58 mg of powdered zinc is added and the resulting mixture is left to stir for 3.5 hours. The reaction medium is filtered through clarcel, washing being carried out with 100 ml of methanol. The filtrate is evaporated to dryness under vacuum and chromatographed on silica gel (15-40 μm), elution being carried out with a gradient of methanol (2% to 7% v/v) in dichloromethane. 116 mg of 5-quinolin-3-yl-9H-pyrrolo[1,2-a]indol-9-ylamine acetate are obtained in the form of a brown solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. waitthe resulting mixture is left
  3. waitthe resulting mixture is left
  4. stirringto stir for 3.5 hours
  5. filtrationThe reaction medium is filtered through clarcel
  6. washwashing
  7. customThe filtrate is evaporated to dryness under vacuum
  8. customchromatographed on silica gel (15-40 μm), elution

Sources & evidence

ORD record
ord-6c0dd93a20bd4e7aae380c79fc03a4a0
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

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